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87303

Sigma-Aldrich

Tetrahexylammonium hydrogensulfate

≥98.0% (T)

Synonym(s):

THAHS, Tetra-n-Hexylammonium Hydrogen Sulfate

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5 G
$97.90
25 G
$461.00
100 G
$1,460.00

About This Item

Linear Formula:
[CH3(CH2)5]4N(HSO4)
CAS Number:
32503-34-7
Molecular Weight:
451.75
Beilstein:
4629729
EC Number:
251-069-0
MDL number:
MFCD00037675
UNSPSC Code:
12352116
PubChem Substance ID:
57653236
NACRES:
NA.22

$97.90

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Quality Level

100

Assay

≥98.0% (T)

form

crystals

mp

98-100 °C (lit.)

SMILES string

OS([O-])(=O)=O.CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC

InChI

1S/C24H52N.H2O4S/c1-5-9-13-17-21-25(22-18-14-10-6-2,23-19-15-11-7-3)24-20-16-12-8-4;1-5(2,3)4/h5-24H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1

InChI key

RULHPTADXJPDSN-UHFFFAOYSA-M

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Application

Tetrahexylammonium hydrogensulfate can be used as a phase-transfer agent to facilitate certain organic reactions in a two-liquid phase system. For example:
  • Epoxidation of α,β-unsaturated ketones in a biphasic dichloromethane/water mixture using sodium perborate.[1]
  • Transfer hydrogenolysis of aryl bromides by aqueous sodium formate catalyzed by palladium-triphenylphospine.[2]
  • Carbonylation of benzylic and allylic bromides to synthesize carboxylic esters.[3]

Other Notes

Lipophilic phase transfer catalyst. Most efficient catalyst in ruthenium-catalyzed reactions[4]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3115
BCCK1911
BCCH1927
BCCJ4315
BCCJ5170

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R. Bar et al.
Tetrahedron Letters, 22, 1709-1709 (1981)
Catalytic carbonylation of benzylic and allylic bromides by a rhodium zwitterionic complex under phase transfer catalysis conditions
Amaratunga S and Alper H
Journal of Organometallic Chemistry, 488, 25-28 (1995)
Transfer hydrogenolysis of aryl bromides by sodium formate and palladium?phosphine catalyst under phase transfer conditions.
Bar R, et al.
J. Mol. Catal., 16(2), 175-180 (1982)
Epoxidation of ?, ?-unsaturated ketones with sodium perborate.
Straub T S, et al.
Tetrahedron Letters, 36(5), 663-664 (1995)
Zeynep S Teksin et al.
Journal of controlled release : official journal of the Controlled Release Society, 116(1), 50-57 (2006-10-20)
Parallel Artificial Membrane Permeability Assay (PAMPA) is a method to screen drug candidates for membrane permeability. The objective was to characterize the transport of a model weak base, metoprolol, across a three lipid-component PAMPA system (denoted A-PAMPA, for anionic-PAMPA) and
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